Sodium Iodide → (2-(4-Bromophenoxy)ethyl)dimethylamine

HRID 1383924Notes

Reaction equation

HRID 1383924 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl.[CH3:10][N:11]([CH2:13][CH2:14]Cl)[CH3:12].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(C(C)=O)C>[CH3:10][N:11]([CH2:13][CH2:14][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:12]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 78084-BromophenolHCID 10796Cesium carbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 213877(2-(4-Bromophenoxy)ethyl)dimethylamineYield 74%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-bromophenol (5.0 g, 28.9 mmol), 2-(N, N-dimethylamino)ethyl chloride, hydrochloride (6.24 g, 43.4 mmol), sodium iodide (600 mg, 4 mmol), cesium carbonate (28 g, 86.7 mmol) and methyl ethyl ketone (120 ml) was heated to reflux for 4 h. After cooling to r.t., the mixture was filtered and washed with acetone. The combined filtrates were concentrated in vacuo, and the residue was chromatographed on silica gel (dichloromethane/methanol 95:5 to 90:10) to give a pale yellow liquid. Bulb-to-bulb distillation (80-84° C./0.05 mmHg) afforded the title compound (5.19 g, 74%) as a colorless liquid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. filtrationthe mixture was filtered
  4. washwashed with acetone
  5. concentrationThe combined filtrates were concentrated in vacuo
  6. customthe residue was chromatographed on silica gel (dichloromethane/methanol 95:5 to 90:10)
  7. customto give a pale yellow liquid
  8. distillationBulb-to-bulb distillation (80-84° C./0.05 mmHg)

Sources & evidence

ORD record
ord-bbbd996fcc264e6cbcbdcc619608a02f
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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